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Born Michael DeVinko in Garfield, New Jersey on September 24, 1934, he was the youngest of three children of Mary and Michael DeVinko. He grew up in a musical family, playing the piano and accordion. "My parents encouraged him to be a musician, " recalls his sister, Caroline Tassely. "He was very talented and played popular music in clubs in the fifties and sixties."

He played the piano at "Jilly's", a top Manhattan nightclub that Frank Sinatra used to frequent. Deans later worked as the manager of the popular discothèque "Arthur," where notables such as Aristotle and Jacqueline Onassis could be found. In 1966, according to Deans' book "Weep No More, My Lady," he met world-renowned actress and singer Judy Garland at her hotel in New York. A mutual friend of theirs asked Deans to deliver a package of stimulant tablets to Judy. Deans recalled that she seemed cordial but disoriented. Judy's children Joe and Lorna were present, and Deans felt it appropriate, under the circumstances, to introduce himself as a doctor. After three years of intermittent dating, Deans proposed and they were married on March 15, 1969, in London. Deans tried his best to promote Judy's career toward the end of her life, but, as previous husbands had found, it was impossible to control Garland's excessive use of prescription drugs. Deans discovered Garland dead on the morning of June 22, 1969. Although many obituaries at the time stated that Judy was found on the floor of their bathroom, Deans stated that he found her seated on the toilet. The coroner's autopsy later determined she died from an accidental, incautious overdose of barbiturates.[citation needed]

Following Garland's death, Deans co-authored Weep No More, My Lady, a biography of Garland written with Ann Pinchot. The book includes autobiographical elements of Deans' pre-Garland life and their time together. The book was published in 1972 by Hawthorn Books with paperback editions issued by Pyramid Books.